HU209489B - Process for the preparation of n-formyl-l-aspartic anhydride - Google Patents

Process for the preparation of n-formyl-l-aspartic anhydride Download PDF

Info

Publication number: HU209489B
Authority: HU; Hungary
Prior art keywords: aspartic acid; acetic anhydride; added; molar equivalents; aspartic
Prior art date: 1988-02-12

Application number

HU904595A

Other languages

English (en)

Hungarian (hu)

Other versions

HU904595D0 (en

HUT58046A (en

Inventor

Robert Erickson

John B Hill

Hugh Ljr Dryden

Original Assignee

Nutrasweet Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-02-12

Filing date

1990-07-24

Publication date

1994-06-28

1990-07-24 Application filed by Nutrasweet Co filed Critical Nutrasweet Co

1990-07-24 Priority to HU904595A priority Critical patent/HU209489B/hu

1990-12-28 Publication of HU904595D0 publication Critical patent/HU904595D0/hu

1992-01-28 Publication of HUT58046A publication Critical patent/HUT58046A/hu

1994-06-28 Publication of HU209489B publication Critical patent/HU209489B/hu

Links

DFTMVZIUYVECNW-VKHMYHEASA-N n-[(3s)-2,5-dioxooxolan-3-yl]formamide Chemical compound O=CN[C@H]1CC(=O)OC1=O DFTMVZIUYVECNW-VKHMYHEASA-N 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 96
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 51
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 34
229960005261 aspartic acid Drugs 0.000 claims abstract description 32
235000019253 formic acid Nutrition 0.000 claims abstract description 26
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 25
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims abstract description 23
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims abstract description 23
238000006243 chemical reaction Methods 0.000 claims abstract description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 25
239000011541 reaction mixture Substances 0.000 claims description 25
150000003333 secondary alcohols Chemical class 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 3
241001169121 Gabriella Species 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
235000003704 aspartic acid Nutrition 0.000 description 9
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000000395 magnesium oxide Substances 0.000 description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 5
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
229940024606 amino acid Drugs 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
108010016626 Dipeptides Proteins 0.000 description 2
RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229960005190 phenylalanine Drugs 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
HEHIABBKSZTAOI-REOHCLBHSA-N (2S)-2-(fluoroamino)butanedioic acid Chemical compound OC(=O)C[C@H](NF)C(O)=O HEHIABBKSZTAOI-REOHCLBHSA-N 0.000 description 1
GWKOSRIHVSBBIA-REOHCLBHSA-N (3s)-3-aminooxolane-2,5-dione Chemical compound N[C@H]1CC(=O)OC1=O GWKOSRIHVSBBIA-REOHCLBHSA-N 0.000 description 1
125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
-1 carbobenzoxy, tert-butoxycarbonyl Chemical group 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Furan Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU904595A 1988-02-12 1990-07-24 Process for the preparation of n-formyl-l-aspartic anhydride HU209489B (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
HU904595A HU209489B (en)	1988-02-12	1990-07-24	Process for the preparation of n-formyl-l-aspartic anhydride

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15626888A	1988-02-12	1988-02-12
HU904595A HU209489B (en)	1988-02-12	1990-07-24	Process for the preparation of n-formyl-l-aspartic anhydride

Publications (3)

Publication Number	Publication Date
HU904595D0 HU904595D0 (en)	1990-12-28
HUT58046A HUT58046A (en)	1992-01-28
HU209489B true HU209489B (en)	1994-06-28

Family

ID=22558839

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU904595A HU209489B (en)	1988-02-12	1990-07-24	Process for the preparation of n-formyl-l-aspartic anhydride

Country Status (14)

Country	Link
EP (1)	EP0466959B1 (de)
JP (1)	JP2611047B2 (de)
KR (1)	KR0185410B1 (de)
CN (1)	CN1058784A (de)
AT (1)	ATE133168T1 (de)
AU (1)	AU649623B2 (de)
BR (1)	BR9007647A (de)
DE (1)	DE69024952T2 (de)
DK (1)	DK0466959T3 (de)
ES (1)	ES2081877T3 (de)
GR (1)	GR3018712T3 (de)
HU (1)	HU209489B (de)
WO (1)	WO1992000949A1 (de)
ZA (1)	ZA905686B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9007646A (pt) *	1988-02-12	1992-09-15	Nutrasweet Co	Processo em recipiente unico de preparacao de hidrocloreto de -apm,processo de copulacao de anidrido n-formil-l-aspartico com l-fenilalanina e processo de preparacao de isomeros de / -n-formil-l-aspartil-l-fenilalanina
CN102206246A (zh) *	2011-04-18	2011-10-05	吴江	水相合成N-甲酰-α-L-天门冬氨酰-L-苯丙氨酸的方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3933781A (en) *	1973-11-05	1976-01-20	Monsanto Company	Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters
US4508912A (en) *	1982-03-30	1985-04-02	Ajinomoto Company, Incorporated	Process for producing N-carbobenzoxy-L-aspartic anhydride
IT1152488B (it) *	1982-08-06	1986-12-31	Pierrel Spa	Procedimento per la preparazione dell'anidride dell'acido n-formil-l-aspartico
JPS59175484A (ja) *	1983-03-25	1984-10-04	Ajinomoto Co Inc	Ｎ−ホルミルアスパラギン酸無水物の製造法
US4670568A (en) *	1984-12-07	1987-06-02	Ajinomoto Co., Inc.	Process of producing n-formylaspartic anhydride
JPS63154669A (ja) *	1986-12-18	1988-06-27	Mitsui Petrochem Ind Ltd	イミダゾ−ル類の製造工程におけるギ酸の除去方法
JPS62252754A (ja) *	1986-04-24	1987-11-04	Ajinomoto Co Inc	新規アミノ酸誘導体および甘味剤組成物
JPH085912B2 (ja) *	1986-09-04	1996-01-24	味の素株式会社	Ｎ−ホルミルアスパルチル−フエニルアラニンまたはそのメチルエステルの製造方法
US4801742A (en) *	1987-07-17	1989-01-31	W. R. Grace & Co.-Conn.	N-formylation of amino carboxylates with alkyl formates
JPH01100163A (ja) *	1987-10-14	1989-04-18	Mitsui Toatsu Chem Inc	Ｎ−ホルミル−ｌ−アスパラギン酸無水物の製造法

1990
- 1990-07-11 AU AU61506/90A patent/AU649623B2/en not_active Ceased
- 1990-07-11 KR KR1019910700148A patent/KR0185410B1/ko not_active Expired - Fee Related
- 1990-07-11 BR BR909007647A patent/BR9007647A/pt not_active Application Discontinuation
- 1990-07-11 JP JP2511285A patent/JP2611047B2/ja not_active Expired - Lifetime
- 1990-07-11 WO PCT/US1990/003898 patent/WO1992000949A1/en not_active Ceased
- 1990-07-19 AT AT90113843T patent/ATE133168T1/de not_active IP Right Cessation
- 1990-07-19 ES ES90113843T patent/ES2081877T3/es not_active Expired - Lifetime
- 1990-07-19 DK DK90113843.8T patent/DK0466959T3/da active
- 1990-07-19 ZA ZA905686A patent/ZA905686B/xx unknown
- 1990-07-19 EP EP90113843A patent/EP0466959B1/de not_active Expired - Lifetime
- 1990-07-19 DE DE69024952T patent/DE69024952T2/de not_active Expired - Fee Related
- 1990-07-24 HU HU904595A patent/HU209489B/hu not_active IP Right Cessation
- 1990-08-06 CN CN90106907A patent/CN1058784A/zh active Pending
1996
- 1996-01-18 GR GR950403643T patent/GR3018712T3/el unknown

Also Published As

Publication number	Publication date
EP0466959B1 (de)	1996-01-17
JPH05500359A (ja)	1993-01-28
EP0466959A1 (de)	1992-01-22
ZA905686B (en)	1991-07-31
GR3018712T3 (en)	1996-04-30
WO1992000949A1 (en)	1992-01-23
DK0466959T3 (da)	1996-02-12
DE69024952T2 (de)	1996-05-30
ATE133168T1 (de)	1996-02-15
BR9007647A (pt)	1992-09-15
JP2611047B2 (ja)	1997-05-21
AU649623B2 (en)	1994-06-02
CN1058784A (zh)	1992-02-19
ES2081877T3 (es)	1996-03-16
HU904595D0 (en)	1990-12-28
DE69024952D1 (de)	1996-02-29
KR0185410B1 (ko)	1999-06-01
HUT58046A (en)	1992-01-28
AU6150690A (en)	1992-02-04

Legal Events

Date	Code	Title
1996-04-29	HMM4	Cancellation of final prot. due to non-payment of fee
1996-05-28	HNF4	Restoration of lapsed final prot.
2002-04-29	HMM4	Cancellation of final prot. due to non-payment of fee

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HU207286B (en)	1993-03-29	Process for producing melfalane and melfalane-hydrochloride of high purity
HU209489B (en)	1994-06-28	Process for the preparation of n-formyl-l-aspartic anhydride
Fehrentz et al.	1994	Synthesis of chiral N-protected β-amino alcohols by the use of UNCAs
US3467667A (en)	1969-09-16	Tetrahydropyranyl tyrosine n-carboxy (and thiocarboxy)anhydrides
CA2021178C (en)	1998-04-28	Preparation of n-formyl-l-aspartic anhydride
US4945172A (en)	1990-07-31	Preparation of N-formyl-L-aspartic anhydride
US6316660B1 (en)	2001-11-13	Process for producing cyclohexylamino acids
US4673744A (en)	1987-06-16	Method for conversion of β-aspartylphenylalanine derivatives to .alpha.
HU214942B (hu)	1998-08-28	Eljárás N-helyettesített glicin-észterek és glicin, továbbá ezekből indoxil- és indigószármazékok előállítására
US4789757A (en)	1988-12-06	N-formylation of amino carboxylic compounds with formamide
US4025499A (en)	1977-05-24	Preparation of histidine-containing peptides
Nomura et al.	1989	Triphenylstibine oxide–phosphorus (V) sulfide as a novel condensation catalyst system: application to the synthesis of dipeptides
US4897507A (en)	1990-01-30	Method for producing α-L-aspartyl-L-phenylalanine derivatives
PL163892B1 (pl)	1994-05-31	Sposób wytwarzania bezwodnika kwasu N-formylo-L-asparaginowego
US5728888A (en)	1998-03-17	Preparation of hydroxylated benzophenones
CZ282717B6 (cs)	1997-09-17	Způsob přípravy anhydridu N-formyl-L-asparagové kyseliny
US2820781A (en)	1958-01-21	Process for producing amides
US5017690A (en)	1991-05-21	Deblocking N-formyl aspartame compounds
RO109449B1 (ro)	1995-02-28	Procedeu pentru prepararea anhidridei N-formil-L-aspartice
US3668232A (en)	1972-06-06	N-substituted 2-aminomethyl-2{40 -biphenylcarboxylic acid and derivatives
EP0300450B1 (de)	1994-05-04	Methode für die Herstellung von methylester hydrochlorid alpha-L-Aspartyl-L-phenylalanin
CA1318459C (en)	1993-05-25	Imides, a process for their production thereof and a process for the production of dipeptides by using them
US3740386A (en)	1973-06-19	Preparation of peptides
US3340274A (en)	1967-09-05	Hydroxy amino acid derivatives
KR870000271B1 (ko)	1987-02-23	N-[3-[3-(1-피페리디닐메틸) 페녹시] 프로필] 아세톡시 아세트아미드 염산염의 제법